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Asymmetric remote C–CH borylation of aliphatic amides and esters with a modular iridium catalyst

Title	Asymmetric remote C–CH borylation of aliphatic amides and esters with a modular iridium catalyst
Authors	Ronald L. Reyes, Miyu Sato, Tomohiro Iwai, Kimichi Suzuki, Satoshi Maeda, Masaya Sawamura
Magazine	Science
Date	08/20/2020
DOI	10.1126/science.abc8320
Introduction	Site selectivity and stereocontrol present significant challenges in C–C bond functionalisation chemistry, particularly within linear aliphatic saturated hydrocarbon scaffolds. This work reports a highly enantioselective and site-selective catalytic borylation of remote C(sp3)–C(H) bonds, situated beta to the carbonyl group, in aliphatic secondary and tertiary amides and esters. A chiral C–C(H) activation catalyst was modularly assembled from an iridium centre, a chiral monophosphite ligand, an achiral urea-pyridine receptor ligand, and pinacolatoboryl groups. Quantum chemical calculations provide support for an enzyme-like structural cavity formed by the catalyst components, which facilitate substrate binding through multiple noncovalent interactions. The versatile synthetic utility of the resulting enantioenriched beta-borylcarboxylic acid derivatives is also demonstrated.
Quote	Ronald L. Reyes, Miyu Sato and Tomohiro Iwai et al. Asymmetric remote C–CH borylation of aliphatic amides and esters with a modular iridium catalyst. Science. 2020. Vol. 369(6506):970-974. DOI: 10.1126/science.abc8320
Element	Iridium (Ir) , Boron (B) , Carbon (C) , Phosphorus (P) , Nitrogen (N)
Materials	Chemical Compounds
Industry	Research & Laboratory

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